20349-86-4Relevant articles and documents
Studies toward the Total Synthesis of Arylnaphthalene Lignans via a Photo-Dehydro-Diels-Alder (PDDA) Reaction
Wessig, Pablo,Badetko, Dominik,Czarnecki, MacIej,Wichterich, Lukas,Schmidt, Peter,Brudy, Cosima,Sperlich, Eric,Kelling, Alexandra
, p. 5904 - 5915 (2022/04/22)
An efficient method for the preparation of arylnaphthalene lignans (ANLs) was developed, which is based on the Photo-Dehydro-Diels-Alder (PDDA) reaction. While intermolecular PDDA reactions turned out to be inefficient, the intramolecular variant using suberic acid as tether linking two aryl propiolic esters smoothly provided naphthalenophanes. The irradiations were performed with a previously developed annular continuous-flow reactor and UVB lamps. In this way, the natural products Alashinol D, Taiwanin C, and an unnamed ANL could be prepared.
A 5C + 5C Bicycloaromatization Reaction via an Aldol Condensation Cascade: A Regioselective Synthesis of Functionalized Naphthalenes from Acyclic Precursors
Stossel, D.,Chan, T. H.
, p. 4901 - 4908 (2007/10/02)
A regioselective synthesis of naphthalene derivatives 51 was developed by the reaction of 1,3,5-tris(trimethylsiloxy)-1-methoxyhexa-1,3,5-triene (2) with the 1,3,5-tris-electrophiles 50 and trimethylsilyl triflate.Three carbon-carbon bonds are formed in this aldol condensation cascade, where the regiochemistry is controlled by the different reactivities at the sites of the acyclic precursors.